41613-26-7

Basic information

• Product Name: 1,3-DIMETHYL-5-NITROURACIL HYDRATE
• Synonyms: 1,3-DIMETHYL-5-NITROURACIL HYDRATE;1,3-DIMETHYL-5-NITROURACIL MONOHYDRATE;1,3-dimethyl-5-nitrouracil;5-Nitro-1,3-dimethyluracil;1,3-dimethyl-5-nitro-2,4(1H,3H)pyrimidinedione
• CAS NO: 41613-26-7
• Molecular Formula: C₆H₇N₃O₄
• Molecular Weight: 203.15
• EINECS: 255-462-8
• Mol File: 41613-26-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 155-160 °C(lit.)
• Boiling Point: 262.7 °C at 760 mmHg
• Flash Point: 112.7 °C
• Appearance: /
• Density: 1.51 g/cm³
• Vapor Pressure: 0.0107mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 1,3-DIMETHYL-5-NITROURACIL HYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIMETHYL-5-NITROURACIL HYDRATE(41613-26-7)
• EPA Substance Registry System: 1,3-DIMETHYL-5-NITROURACIL HYDRATE(41613-26-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 41613-26-7(Hazardous Substances Data)

Usage

Description

1,3-Dimethyl-5-nitro uracil hydrate, also known as DNBC, is a nitro-substituted uracil derivative characterized by its yellow crystalline solid form. It is soluble in organic solvents and exhibits stability under normal temperatures and pressures. 1,3-DIMETHYL-5-NITROURACIL HYDRATE is recognized for its potential in the synthesis of pharmaceuticals and as a dye precursor, with ongoing research into its applications in treating various diseases and in the development of new materials and chemical processes.

Uses

Used in Pharmaceutical Synthesis:
1,3-Dimethyl-5-nitro uracil hydrate is used as a key intermediate in the synthesis of pharmaceuticals for its chemical properties that facilitate the creation of new drug molecules.
Used in Dye Precursor Applications:
In the dye industry, 1,3-Dimethyl-5-nitro uracil hydrate serves as a precursor, contributing to the development of new dyes due to its chemical structure and reactivity.
Used in Cancer Treatment Research:
1,3-Dimethyl-5-nitro uracil hydrate is used as a subject of research for its potential role in the treatment of cancer, with ongoing studies exploring its effects on various types of the disease.
Used in Infectious Disease Treatment Research:
Similarly, this compound is under investigation for its possible applications in treating infectious diseases, indicating its broad potential in the medical field.
Used in Material and Chemical Process Development:
1,3-Dimethyl-5-nitro uracil hydrate is utilized in the development of new materials and chemical processes, highlighting its versatility in scientific and industrial applications.
It is important to handle 1,3-DIMETHYL-5-NITROURACIL HYDRATE with care, adhering to safety protocols to mitigate potential health and environmental hazards associated with its use.

InChI:InChI=1/C6H7N3O4/c1-7-3-4(9(12)13)5(10)8(2)6(7)11/h3H,1-2H3

Upstream product

• 611-08-5 5-nitrobarbituric acid 
• 74-83-9 methyl bromide 
• 74-88-4 methyl iodide 
• 874-14-6 1,3-dimethyluracil 
• 108047-30-9 3-methyl-5-nitro-1-(p-nitrophenyl)uracil 
• 74-89-5 methylamine 
• 66-22-8 uracil 
• 77-78-1 dimethyl sulfate 
• 934802-64-9 3-methyl-5-nitro-1-phenyluracil 
• 108070-70-8 5,6-dihydro-3-methyl-6-methylamino-1-(p-nirophenyl)uracil methylammonium salt 
• 75-04-7 ethylamine 
• 128039-12-3 1-methyl-1-(3-methylamino-2-nitroacryloyl)-3-(p-nitro-phenyl)urea methylammonium salt 

Downstream Products

• 505-21-5 hexahydropyrimidine 
• 24039-08-5 1,3-dimethylimidazolidine-2,4-dione 
• 64732-10-1 5-hydroxy-1,3-dimethylimidazolidine-2,4-dione 
• 98-92-0 nicotinamide 

Relevant articles and documents

Design, synthesis of 1,3-dimethylpyrimidine-2,4-diones as potent and selective aldehyde dehydrogenase 1A1 (ALDH1A1) inhibitors with glucose consumption improving activity

LDH1A1, one of 19 NAD(P)+-dependent aldehyde dehydrogenases, participates in multiple metabolic pathways and has been indicated to play an important role in obesity and diabetes. In this study, a series of 1,3-dimethylpyrimidine-2,4-diones were designed, synthesized and evaluated as novel selective aldehyde dehydrogenase 1A1 inhibitors. Among them, compounds 46, 50, 53, 56 and 57 exhibited excellent inhibitory activity against ALDH1A1 with IC50 values in the low nanomolar range and high selectivity over ALDH1A2, ALDH1A3, ALDH2 and ALDH3A1. Furthermore, in vitro study demonstrated that compound 57 effectively improved glucose consumption in HepG2 cells compared to compound 1 (CM026).

The impact of 5-substituted uracil derivatives on immortalized embryo lung cells

Background: Pyrimidine-based drugs stimulate tissue regeneration and immunity, two components that need to be improved in a number of respiratory diseases of different etiology (e.g. influenza and asthma). In the present study we investigated relationships between the character of substitutions in the uracil structure and the impact of the respective uracil derivatives on the immortalized lung cells. Methods: The level of cell proliferation, maximum tolerated dose and toxic effect of 5-substituted uracil derivatives (12 compounds) were studied on the immortalized lung epithelial cells and compared with the ones of 6-methyluracil. Results: 5-Carboxyuracil and 1,3-dimethyl-5-carboxyuracil had the lowest cytotoxicity among the studied compounds. Their maximal tolerated dosage values were 5 times higher whereas the proliferation index was increased by 25% and 75%, respectively, compared to 6-methyluracil, known for its positive effects on cell regeneration. Conclusion: 5-Carboxyuracil and 1,3-dimethyl-5-carboxyuracil have the best perspectives for further studies on their biological effects.

Dehydrogenation, oxidative denitration and ring contraction of N,N-dimethyl-5-nitrouracil by a Bacillus nitroreductase Nfr-A1

Nfr-A1, a Bacillus subtilis nitroreductase, catalyzes the nitroreduction of a large panel of aromatic and heterocyclic nitro compounds, except those belonging to nitrouracil class of molecules. Besides nitroreduction, Nfr-A1 exhibits a strong NADH oxidase activity in the presence of oxygen, leading to high concentration of H2O2 (up to 200 μM). In the presence of (N,N)-dimethyl-5-nitrouracil 1 (dim-NU), Nfr-A1 achieves the reduction of dim-NU double bond to compounds 2 and 3 and in parallel the oxidation of dim-NU to the denitrated five membered derivatives 4 and 5. The reduction is catalyzed by the reduced flavin Fl-Red and resembles those catalyzed by dihydropyrimidine dehydrogenases (DPD), during the catabolism of pyrimidines. The oxidative denitration is catalyzed in part by hydrogen peroxide generated through the NADH-oxidase activity, and certainly by the peroxyflavin intermediate Fl-OOH for the other part. The mechanisms of reaction were proposed according to experimental data and literature. These findings together with our previous results on the potential biological role of Nfr-A1, confirm the large spectrum of catalysis supported by this enzyme. The oxidative denitration is sporadically reported in literature and represents a safe and green alternative for the remediation of nitro-compounds.